Category Archives: Discussing Sexual Issues

Sorry about last Monday you guys. As you know I had intended to get this Q&A show earlier in the week, but technical difficulties prohibited that. Not to worry, because here we are now. I have a bunch of very interesting correspondents who are ready to share their sex and relationship concerns with us. And I will do my level best to make my responses informative, enriching and maybe even a little entertaining.

Duke wants to experiment with getting butt fucked, but is afraid to make the first move.

Name: Dan
Gender: Male
Age: 48
Location: Montreal
I’m a late forties year old man who has lived numerous sexual experience in the past, until I met just in the beginning of this past year a wonderful interesting, woman with all the qualities and values that I needed. We started our first sexual experience a few months ago, April. The result was quite a disaster. I wasn’t able to do any penetration on her. She insisted that she has a blockage, and I had no idea about blockage and wanted to leave her place. Now I tried to understand her, but her problem has two factors that I’ve never came across with a woman. One is that if I fucked her she would get vaginitis. She doesn’t have any reaction when I fuck her. However, the scenario with her is the usual. She would get into her closet wear something very daring and sexy and give me a nice blowjob and …swallow. I would usually experience just straight penetration, in any position in my past experience with other women But would this mean that the sexy clothes and asking me if I would cum in her mouth, compensated for her inability to have my penis in her vagina? She asked me that I would have to eat her pussy often so she would feel something. The last time I did I was eating her pussy for two hours with a few breaks until she came. My question is can I take this any longer, and what is the connection with her vaginitis?

Hell, Dan, I don’t know if you can take this any longer or not. What’s clear to me is, things are pretty grim, not just for you but also for your lady friend.

Your story is a little difficult to follow. I’m gonna guess that English is not your first language, right? But here’s what I think you’re trying to say. You are a sexually experienced man in his forties. You’ve recently met an interesting woman that you like very much. Unfortunately, the sex sucks…and not in a good way.

Your friend experiences pain while fucking, but you don’t know why. She says there’s a blockage and tells you that intercourse will only lead to vaginitis, which is an inflammation of the vaginal mucosa and often associated with an irritation or an infection. While this is a pretty common problem, it should not be an every fucking time kinda problem…if you catch my drift. However, this little lady is happy to give you a hummer to make up for this. And just to show you there are no hard feelings — she’ll even swallow your spunk. Well, she’s a trooper that’s for sure! Unfortunately, avoiding the fucking issue won’t solve the mystery of why fucking is a real pain in the pussy.

The two most likely reasons for this painful fucking are: 1) the woman is not aroused enough before the fucking begins, or 2) there is an actual physical condition that might make fucking painful, even if she is aroused.

It’s easy enough to eliminate the second option; all your woman friend has to do is pay her gynecologist a little visit and have her doc take a quick look around. If there is indeed a blockage, as she says there is, a gynecological exam will discover it and end the debate.

That being said, I’d be willing to bet that, in your friend’s situation the first reason is the more likely culprit. This is often the case with pre-orgasmic women and your woman friend sounds like she may very well fall into that category. If your woman friend has lived all her adult life without having an orgasm, she will sure enough be conditioned not to expect one any time soon — either through fucking or by having you eat her out…even for hours. And hey, you’re a trooper too for doin’ that, darlin’!

I’d be willing to speculate that she’s not particularly informed about her own sexual response cycle. Thus she’s unable to provide you much direction on how to pleasure her without discomfort. A woman, particularly a preorgasmic one, must come to full arousal before her partner attempts penetration. A man, on the other hand, needs only to have a stiff dick. This obviously makes them (men) more ready and eager for the old in and out long before their female partner is ready and eager for the same. If you are guilty of this, and there’s a good chance that you are, your woman friend’s body will resist you, even if she desires to make a go of it.

Your woman friend could start getting over this by being better informed about her own sexual response cycle. If she doesn’t know what turns her crank, she can’t expect you to know what to do, even with all of your experience. Once she figures out how her body works, and this information will come best through masturbation, she’ll then be able to instruct you on the subtleties and points of interest of her particular pussy.

Touch is very important to most women, especially in the arousal stage of things. Often women will want to be touched and caressed all over, not just on the sexually charged spots of her body like her tits and pussy. She ought to take you on a little touch tour of her body. Literally, she could take you by the hand and touch herself with your fingers. She should show you the kind of touch she likes in the places she likes to be touched. You guys will need to take your time with this. I can pretty much guarantee you won’t get it the hang of this first time you try.

With her help you’re gonna be able to see her arousal build. She could encourage you to use your lips and mouth as well as your hands. If she’s not fully aroused, her pussy will be dry. But even if she is wet, you ought to use a nice personal lubricant to make her even more slippery and to facilitate penetration. I can’t overstate the necessity of lots and lots of lube.

If you guys follow these simple steps, you will have greater success with your fucking. Your woman friend will experience great pleasure and she will, in turn, be a fount of great pleasure for you. In the end, your woman friend must take the lead in this. She must get to know her own body first, so she can teach you about it next.

Name: DJ
Gender: Male
Age: 39
Location: Northern Minnesota
I’ve been in a gay relationship for almost 12 years now. My partner and I are very happy and I’ve been thinking about adding a new addition to our relationship just to spice things up a little bit. We were looking through the gay personals online and we found this guy who happens to be a patient of mine. He’s just our type. He’s a handsome, well built bear in his early 40’s. We’re considering contacting him, but we’re not sure if that would be crossing a line. So if you could give us some advice that would be great. Thanks.

Ahhh let’s see, the short answer is; yes, you would be crossing a line. Offering your patient a tryst, with you and your hubby would indeed be way on the other side of that line. Ya know the old adage, “Don’t shit where you eat?” Well, this is exactly like that, only completely different.

While I’m happy to support you and your man as you work toward opening your relationship by adding a playmate or two, the current object of your desires is, to my mind, inappropriate. I think it’s always ill advised for professional people in general, and healing and helping professionals in particular, to get involved (romantically or otherwise) with their clients or patients. There’s always the possibility of a conflict of interest, but more importantly, there’s the issue of propriety.

That’s not to say that this sort of thing doesn’t happen all the time. It does. But I think there are significant potential problems for you, the professional, as well as this other guy, your patient.

When I’m faced with a similar dilemma in my own life, I sit myself down with pen and paper and write out all the pros and cons of a hook-up, even a casual one, with someone I have a professional relationship with. Regardless of whether I know the guy through my therapy practice or by way of my production company; it’s all the same for me. These are lines I should not cross. But sometimes I need to remind myself of that.

So with my pad and pen at the ready I quickly jot down the “pros” of the hook-up. These are always so easy to enumerate. He’s hot, he’s charming, he’s fun to be around, he’s got a great personality and a wonderful sense of humor and he’s single. Hell, he may even be hot for me…although that’s less likely these days, now that I’m an old fuck. But hey, it could happen! So if I only consider the “pros” this appears to be a match made in heaven. What could possible go wrong with this idyllic picture? WAIT!

That’s where the “cons” come in handy. They are the bane of my existence, but they also keep me out of harms way. If I’m struggling to come up with a list of “cons”, I simply conjure up, in my fevered little mind, the worst relationship I’ve ever had. Frankly, this isn’t a particularly difficult thing to do, because I’ve had some duesies in my time, don’t cha know. The reason I let my mind dredge up the sordid past like this is so that I can remember how bad things can get when a sex connection goes south. I do this to create a worst-case hook-up scenario so that I can imagine what it would be like if the guy in question was not just an unfortunate choice on my part, but he was also a client or porn pup on the rise.

With just this little mental prompting my “cons” category begins to grow and grow. This exercise pretty much puts the kybosh on my ardor and I happily forgo the pleasure of the company of the man in question. Is it possible that I’m overreacting, that the hook-up could have turned out to be a sheer delight? Absolutely! But, being the kind of guy I am, with the bum luck that I have, I’d just as soon not take the chance that it won’t. I have a reputation, checkered as it might be, to uphold. And screwing around with the wrong guy is bad enough; I don’t need the added complication of him thinking that I took advantage of him given my professional association with him.

I invite you to do the same sort of exercise yourself, DJ. First create a column of “pros.” Why does this forty-something, handsome, well-built bear patient of yours with the online profile make a great candidate for a playmate. I’ll bet that you and the hubby already have this all figured out. Now, create your “cons” column. Try to imagine all the awful things that could happen as a result of a sex connection that goes bad — ya know, the jealousy, the bitchyness, the backbiting, the rumors, stuff like that. And when you consider that he’s being invited to a manage-a-trois, well you can triple the risk factor. Like I said, the object here is to create the worst-case scenario. Screwing around with the wrong guy is bad enough; you certainly don’t need to add the complication of him thinking you took advantage of him given your professional association with him. If things go bad and he brings this little encounter to the attention of the medical board, you’d be in a heap of trouble.

Of course there is always the option of terminating your doctor/patient relationship before the fuck. In this case I advise there be at least a two-month hiatus between the end of your professional relationship and the start up of the sexual relationship. However, if I was your patient, and you offered me this option, I’d choose to maintain the professional connection we have. I’d be flattered by your interest in me, but I’d know that it’s much harder to find a good doc than it is to find a sweet bone….even in northern Minnesota.

It’s time for another Q&A show. This time around, I have a really great bunch of correspondents who share their sex and relationship concerns with us. And I go out of my way to make my responses informative, enriching and maybe even a little entertaining.

Joy is unhappy because her BF is into the meth and now their sex life is in the toilet.

AH said something really terrible to his GF while he was drunk, now he’s paying the price.

Then I riff on a handful of effective communication techniques.

Reba says her 6-year-old son is a nancy-boy. I put her straight and tell her to visit this site.

Jackson got himself a dose of the clap, and now he has to tell all his lady friends.

My, my, my! It’s been six whole weeks since our last Q&A show. That’s not good. Because, ya know what? I have a huge backlog of very interesting questions from the sexually worrisome. And this time around, all my correspondents are men. Why, that almost never happens. I trust you will find my responses will educate, enrich and maybe even entertain. With a little luck, I’ll even have just enough time to do a product review. Sound fun? I think so too.

Tyler is straight but has the urge to stuff his ass.Paul has polio, but he still wants to jerk-off.Robert and his partner are having big time relationship problems.John need more sex than he’s getting at home.Steven is pulling his pud a lot, now some of the sensations are gone..Mike is having extreme muscle spasms after he cums.
Finally we review the Fat Boy Cock Sheath.